


I Like To Watch

by JackTrades



Series: I Like To Watch [1]
Category: Supernatural
Genre: Dirty Talk, F/M, Masturbation, Multi, Oral Sex, Other, PWP, Plot What Plot/Porn Without Plot, Porn Watching, Rough Sex, Season 1, Voyeurism, Wincest - Freeform, but they have not addressed how messed up their relationship is yet
Language: English
Status: Completed
Published: 2015-02-19
Updated: 2015-02-19
Packaged: 2018-03-13 17:48:01
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 3,321
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/3390611
Author URL: https://archiveofourown.org/users/JackTrades/pseuds/JackTrades
Summary: <blockquote class="userstuff">
              <p>When Sam accidently walks in on Dean jerking off, he invites Dean to watch him have sex with a girl</p>
            </blockquote>





	I Like To Watch

Dean leisurely made his way into the motel room from the bathroom after his shower.  The latest job was complete early this morning, but the brothers had decided to stay in town another day to search for another case.  The Midwest region seemed to have a lot more activity than usual.  No sense heading anywhere until they caught their next haunting or slashing or rash of disappearances.  Dean was starting to doubt they’d ever hear back from dad, so might as well keep helping people until he decided to resurface. 

 

Sam had left several hours ago to go research at the local library and called to let Dean know he’d probably work through dinner. That was Dean’s cue to grab some greasy food (bonus that Sam wasn’t there to bitch about health and other crap), get a few six packs, and kick back for a few hours.  Normally, Dean would be out at a bar drinking or hustling pool or picking up a date for the night… or all three. But they were pretty set with cash and Dean knew from experience to not go hustling if he wasn’t particularly feeling like doing it.  Sam’s absence gave Dean something he was long overdue for, _me time_.

 

Dean took a quick glance at the clock, 7:13, excellent. The library was open until 8:00 and it would take Sam at least ten minutes to get back to the room. That left Dean with about one hour to treat himself to some porn and a long, lazy jerk off session… a luxury he was not about to waste.  He usually was in favor of picking up a good looking woman to blow off some steam, but doing it himself would never lose its appeal or merits.

 

Sam had left his laptop in the room. Dean grabbed it and situated himself on the bed, sitting with pillows propped against the headboard to support his back while he stretched his legs out on the bed.  He booted up the laptop and went to his favorite free porn clips site.  He went to the categories and searched for several minutes before he found one a clip that would be long enough for his intentions.  From the thumbnail it was perfect: a big-breasted Asian girl with a ponytail.  Description had it tagged as masturbation with toys video, ninety-six percent of other users recommend it, and it was an eighteen-minute clip.  _Awesome._

 

As he clicked the link and let it begin to load, he rearranged himself to get the screen to a good spot without hindering access to his dick.  He reached down and shoved his sweatpants and boxers to the middle of his thighs, spread his legs a little more, and laid the laptop just above his knees, angling the screen for a better view.  He hit play when the video was loaded halfway.  It started with panning up from the girl’s feet to her face; she’s dressed in heels, knee high socks, a very short plaid skirt, and a white button-down shirt with her bra and generous amount of her breasts showing.  She was probably in her early- to mid-twenties, just right in Dean’s opinion.  She moved side to side in time with the music in the clip, though Dean was never really sure if they played music when these clips were filmed or if it just worked out that all the girls can do a sexy dance to the music the producers were going to use anyway.  Either way Dean’s dick was definitely twitching in interest.  He palmed himself without putting any real pressure into the act.  After 40 seconds of following her dance in place, the clip faded into the girl sitting on a couch, still dressed, and the man behind the camera is asking her questions. Dean huffed in annoyance and leaned toward the laptop to advance the clip to where the talking stops. If he wanted to know about a girl and watch her get off, he’d go to the damn bar and get her off himself!

 

He jumps the clip to about six minutes in where the girl is up off the couch and slowly stripping.  She starts with the shirt, tossing it aside and pushing her breasts together, rubbing around the lacy edges of her black bra and pushing them up impossibly higher before shrugging off the left bra strap. Dean is transfixed on the screen as the girl does the same with the right and unhooks the front clasp on the bra to release her full, firm tits from their confines.  Her nipples are already hard and perky. Dean starts stroking himself slowly, at an even pace from base to just below the head and back. She jiggles her breasts with her hands and gives a sensual smile to the camera for several seconds before turning around.  She arches her back and bends slightly while the camera comes down a little more, showing her black thong underneath her plaid skirt.  She hikes the skirt up to her waist and begins toying with the elastic sides of the thong.  She would begin to pull it down then back up, all while subtly shaking her small but firm looking ass.  When she finally pulled the thong down to her thighs, Dean couldn’t stop the groan that escaped his lips. He couldn’t see her holes yet, but he could tell she was wet.  That was enough to get Dean to slightly quicken the pace of his hand.

 

In the clip, the girl goes from standing to leaning back on the couch facing forward.  One leg bent on the couch and the other still on the floor, still wearing the socks, heels, and skirt, she slowly moves her hand down to her pussy. No pubic hair, as Dean assumed, it’s kind of a happy surprise if he finds a porn clip with a girl that isn’t completely shaved.  That doesn’t bother him, but he’s oddly turned on if he does see some well-maintained hair, like a happy surprise.  The camera changes angles again to zoom in on her spread legs.  She spreads herself and lets the camera get very close, Dean groans again when she spreads her lips wide enough for him to see the glistening pink inside of her.  She resumes her movements when the cameraman compliments how good her pussy looks.  She rubs her clit with one hand while the other moves to her hole, slipping two fingers in. She keeps a slowish pace, languidly moaning, before stopping to change her position.  Leaning over the edge of the armrest, knees on the couch and spread fantastically wide, Dean watches as she picks up a bright pink vibrator from the floor.  She slides it up and down the crack of her ass, moaning and looking lustfully at the camera. After some teasing buildup, she finally slides the tip of the toy into herself, letting out a genuine moan. Dean was helpless to do anything but thrust into his fist at the same pace as she thrust the toy into herself. She was building closer and closer to her orgasm…

 

_THAT was the point he had to walk in…_

Sam burst through the door of the motel room with much more zeal than usual.  Dean certainly didn’t squeak as he simultaneously panicked and felt enough embarrassment to turn his cock soft in his hand midthrust. 

 

For his part, Sam didn’t notice.  In fact, he was thoroughly distracted by his _companion_ while he sloppily made out with her in the doorway of the room.  She was in knee high boots and a modest, but tight fitting dress.

 

“DUDE!” was all Dean could muster as a response as he scrambled to cover himself, in some false sense of preserving his own dignity.

 

Sam tore himself away from the petite brunette with him, legitimately shocked that his brother was in the room at all, much less so early in the evening.  “Dean, I…” the conflict of desire for the girl with him and slight embarrassment at his older brother catching him all over a girl warring on his face, “I… I didn’t realize you’d be here.  I assumed you’d go to the bar when I said I would be at the library…”

 

“Well. I didn’t go to the bar.  But hey, it looks like you have company so give me a second and I’ll clear out…” Dean still carried the weight of guilt about Jess, and as far as he knew, Sam didn’t let himself be with anyone since her death. Dean could at least clear out and let Sammy have a good night and lose himself in sex.

 

As Dean spoke he noticed Sam whispering something to his busty date for the night.  She blushed a bit, then looked at Dean with what could only be described as hungry desire.  He definitely wasn’t expecting it when she spoke up. “Well, you were in the middle of something…” Sam resume groping her as she continued, “… maybe you’d like to stay and watch instead?”

 

And damn if that didn’t hit Dean like a freight train. They had done this before, him and Sam.  When Sam was getting old enough to realize that all girls don’t have cooties, Dean practically insisted that he learn how to properly please a woman by watching him with girls a few times.  And Sam, bookworm that he is, was an adept student, curious to learn what Dean would teach him. It wasn’t often or even a regular thing, maybe three or four times when Sam was a teenager.  Definitely not since Sam left, not since Dean dragged him back from Stanford.  And yet here they were, Sam and his attractive lady friend offering him a live show to get his rocks off… well, really, he was about to blow when Sam burst in crashing his boner anyway… if anything this was reparation.  “Well, who could turn down an offer like that, darling? I’ll just stay here then.” The husk in his voice surprised even Dean as he said that.

 

It was a little bit of a blur from there. Dean absently noted that the girl was an employee at the library that they saw when they were researching what ended up to be a quick salt and burn in this town.  He was more intently focused on Sam’s focused determination to get her out of her clothes as fast as possible without breaking from the crushing kiss he was giving her.  At some point he did pause to toe off his shoes and toss his shirt aside, she seemed to be on the same page, sitting on the bed to unzip and remove her boots.  That proved to be either a horrible or fantastic move on her part.  By the time Sam saw her sitting on the bed, Dean could’ve sworn Sam outright _growled_ as he approached.  He grabbed the bottom of her hiked up dress, whipping it up over her head so quickly she seemed disoriented.  He didn’t even bother with the bra, although Dean had reason to believe her breasts were glorious.  Sam had a single-minded goal in his head though.  As he discarded the dress off to the side, he dropped to his knees on the motel floor, between the beds, and roughly grabbed her hips to pull her forward onto the edge of the bed, facing Dean.  Sam grabbed the edge of her cotton panties with his teeth and dragged them down to her knees, where he let his hands take over ripping them the rest of the way off.  Giving the girl no time to process what was happening, Sam dove headfirst between her legs. He licked a long stripe over her hole and clit before flicking his tongue several times over her clit. She threw her head back in shocked pleasure and moaned loudly.  Just like that, Dean’s fading erection was very much back in the game.

 

Sam, in Dean’s opinion, was completely merciless as he ate this girl out. He licked, sucked, even bit at her until he decided thrust his fingers into her.  He didn’t waste time building up; no, he was on a mission.  Once he thrust his two fingers in a few times he crooked them against that bundle of nerves insider her walls and didn’t let up. She was panting and moaning so loud that Dean was sure the management of the motel would be calling the room to tell them to keep it down.  In the midst of it Sam surprised Dean yet again when Sam spoke to her, “Say _his_ name when you come. I want you to scream Dean’s name,” and continued his assault of her G-spot until the squelching sound and panting was all Dean heard in the room.  At some point between the whirlwind of lost clothes and this point where the girl was writhing on the bed in front of him, Dean had started stroking himself again, leaking fairly rapidly from the scene unfolding in front of him. Sam kept up his movements and Dean realized he wasn’t talking to the girl, he was talking to him, “Yeah, look at her, Dean.  Look at how surprised she is by how good this feels.  Bet she’s never had someone made her squirt before…” Dean and the girl both moaned at that.  A few more hard strokes of his fingers inside her and she was gushing over Sam’s hand, screaming, “DEAAAAN!” as she was told to do.   Sam kept up his movements, forcing a second gush from her that had her legs quaking uncontrollably.  Dean had to grip the base of his cock like a vice to keep from coming right then and there.  He knew if he waited to see how this played out it would be worth his while…

 

Sam sat back on his heels and lewdly sucked on his fingers when she spoke up, “Please, fuck me Sam…” This made Sam smirk in a way that only making a woman orgasm hard could, he looked right at her with lust blown eyes and responded, “Let me just get a condom from my bag and we can get to that…”

 

Dean would laugh at this bad porn dialogue unfolding in front of him if it wasn’t getting him off so much.

 

Sam grabbed a condom and a tube of lube from his bag. Before returning to the bed, he dropped his jeans and boxers in one swoop and kicked them to the side. He ripped the condom from the wrapper and rolled it on.  When he reached the bed he casually lay on his back and stretched out with his head on the pillows.  He squirted a generous amount of lube into his palm and started slicking himself up. “If you want to give yourself some time to adjust, I’ll give you a minute,” then leaned in to whisper, but still loud enough for Dean to hear, “And then I’m gonna fuck you until you forget your own name.” She visibly shuddered at that and was more than eager to mount Sam.

 

He held the base of his erection steady as she slowly sank down on him.  She got just past the head when she lifted up and changed the angle of her hips. She sank down again, getting about halfway before she was panting.  Sam was true to his word, giving her a few minutes to bob up and down on his cock with no participation from him.  But eventually she began rolling her hips and bouncing eagerly, a sure sign that she was now comfortable with Sam’s size. 

 

Seizing this moment, Sam made several moved at once. One hand grabbed roughly at the back of her neck and brought her crashing down for a kiss that was way more tongue and teeth and possession than before.  He bent his knees slightly and planted his feet on the mattress. His free hand gripped both of her wrists and held them firmly together behind her back as he began fast and hard, almost violent, thrusts into her.  For her part, the shock was obvious, but the level of arousal and bliss was even more apparent.  Sam quickened his pace and let go of her head in favor of grabbing a fistful of the flesh on her ass as he thrust into her.  Dean could tell she was close to another orgasm and as she crashed over the edge, Sam lifted her entirely off his dick so she could gush onto him, fluid running down to his balls and on his legs.  That was all it took for Dean, seeing Sam throw this girl headlong into another orgasm then continue thrusting into her was enough. He came in thick ropes over his hand and stomach as Sam fucked her through the aftershocks of her orgasm.

 

When it seemed the girl was over stimulated, Sam stopped and rolled her off of him.  He stood up and walked to the foot of the bed.  He then essentially manhandled the woman into a position he wanted. He flipped her and pulled her down the bed, pushed up onto hands and knees temporarily, before he placed a rough, authoritative hand on her upper back and forced her top half onto the mattress.  He kept his hand planted on her back and gripped his shaft with the other hand to guide it into her.  After the first careful insertion, Sam set an outright brutal pace, fucking her into the mattress. He didn’t seem to notice Dean getting up from his bed and going to the bathroom to clean himself up.

 

Dean made a mental note to talk to Sam about how rough he was with girls in bed.  Rough sex was never Dean’s thing.  When he got a woman alone he wanted to slowly and sensually take them apart and give them pleasure until they begged him to stop.  With Sam, it seemed more like he wanted to split them open, bruise them, and make them feel empty without his cock. Not that this girl wasn’t clearly enjoying it, but he didn’t get the appeal of the roughness.

 

As Dean was in the process of saturating a spot where come had gotten onto the leg of his sweatpants, he could hear the loud, escalating grunts from the other room signaling that the end was near. He was still cleaning up when he heard Sam finish.  After some undecipherable murmuring, he heard what he assume to be Sam licking or fingering her to one more orgasm… damn, he had lost count of it, it was either five or six total… he’d have to high five Sam at a more appropriate time for his level of respectable sexual prowess.  He made the conscious decision to remain in the bathroom until he heard the murmuring pick up again and the sound of shuffling clothing before the door of the room opened and closed.

 

Dean finished washing his hands and took several deep, calming breaths before going back into the room.  It reeked like sex in there.  Sam had since pulled his jeans back on and was sprawled across Dean’s bed.  “You’re welcome,” Sam said with a shit-eating grin.

 

“Get the hell out of my bed! You’re crazy if you think I’m sleeping on a wet spot without getting my dick wet!” Dean barked in response.

 

Sam smirked, laughing softly, victoriously, to himself and began stripping his bed sheets before digging in his duffle for his pajamas and heading into the bathroom to shower.  While Sam was up, Dean opened the windows to let the room air out. He’d be lying if he said this wasn’t one of the most awesome, unexpected surprises of his life. And, hey, maybe he could repay Sammy boy the favor and show him the finer points of gently driving a girl crazy with sex in the not-so-distant future.

**Author's Note:**

> I'm a long time fan fiction lurker, but this is my first completed fic. And definitely my first time sharing one. All constructive feedback is greatly appreciated!


End file.
